Abstract
A new pregnane steroid, 1, and three known analogues 2–4, have been isolated from a gorgonian Carijoa sp. collected from the South China Sea. The planar structure and relative configuration of 1 were elucidated from comprehensive spectroscopic data. Its absolute configuration was determined by application of the modified Mosher method. Compounds 1, 3 and 4 exhibited cytotoxicity against the human hepatoma cell line Bel-7402, with IC50 values of 9.33, 11.02 and 18.68 µM, respectively. Additionally, compound 1 exhibited promising antibacterial activity against Pseudomona puido, with a MIC value of 31 nM, which is approximately 5-fold more potent than ciprofloxacin (MIC = 156 nM).
Highlights
Steroidal compounds from marine organisms possess a wide array of unusual structures
Pregnane steroids characterized by an uncommon vinyl side chain represent a minor group of metabolites, and octocorals appear to be their most prolific source [1,2,3]
Following the literature [16], the results indicated that the absolute configuration of C-15 was
Summary
Steroidal compounds from marine organisms possess a wide array of unusual structures. Chemical investigation on the active extract led to the isolation of four pregnanes with a 3-one framework: 15β-hydroxypregna-1,4,20-trien-3-one (1), 15β-acetoxypregna1,4,20-trien-3-one (2) [13], 18-acetoxypregna-1,4,20-trien-3-one (3) [13], and pregna-1,4,20-trien3-one (4) [14,15] (Figure 1). Their structures were elucidated by NMR spectroscopic methods and comparison with data previously reported in the literature. Among these isolated compounds, 1 is a new pregnane steroid
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